Compositions comprising non-crystalline forms of cannabidiol

ABSTRACT

Various aspects of this patent document relate to liquid compositions comprising cannabidiol, which have either freezing points or glass-liquid transition temperatures less than the melting point of pure cannabidiol.

CROSS-REFERENCE TO RELATED APPLICATIONS

This patent application claims priority to U.S. Provisional PatentApplication No. 62/839,564, filed Apr. 26, 2019, and U.S. ProvisionalPatent Application No. 62/845,231, filed May 8, 2019, each of which isincorporated by reference in its entirety.

BACKGROUND

Cannabidiol exists in a crystalline form at room temperature, which hasa melting point of 151 degrees Fahrenheit (66 degrees Celsius).Crystalline cannabidiol lacks robust bioavailability, for example,because the human body is incapable of melting it. The pharmaceuticalEPIDIOLEX® contains cannabidiol dissolved in sesame seed oil to increasebioavailability.

Consumers also vaporize and inhale cannabidiol to increasebioavailability. Cannabidiol crystallization confounds vaporization inelectronic cigarettes and vaporizers because crystallization inhibitsthe flow of cannabidiol toward a heating element. Prior art methods toinhibit the crystallization of cannabidiol for use in electroniccigarettes and vaporizers include the dissolution of cannabidiol inorganic solvents such as propylene glycol, glycerol, and triglycerides.Organic solvents dilute the cannabidiol, however, and present unknownhealth risks. Improved cannabidiol formulations are therefore desirable.

SUMMARY

Various aspects of this patent document relate to liquid compositionscomprising cannabidiol, which have freezing points or glass-liquidtransition temperatures less than the melting point of pure cannabidiol.

DETAILED DESCRIPTION

This patent document discloses that the melting point of cannabidiol canbe lowered by dissolving a small amount of an organic solute in liquidcannabidiol. The melting point of cannabidiol can be reduced to lessthan 70 degrees Fahrenheit (or less than 21 degrees Celsius), forexample, to provide concentrated cannabidiol compositions that areliquids at room temperature. This discovery allows novel productsincluding concentrated cannabidiol vape oil.

Various aspects of this patent document relate to a compositioncomprising cannabidiol. The term “cannabidiol” refers to2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol.

In some embodiments, a composition comprises cannabidiol at aconcentration of 50% to 99.5% by mass and one or more solutes selectedfrom terpenes, terpene alcohols, and terpenoids at a combinedconcentration of 0.5% to 40% by mass, in which the one or more solutesare dissolved in the cannabidiol; the composition has either a freezingpoint or a glass-liquid transition temperature; and the freezing pointor the glass-liquid transition temperature is either at least 50 degreesFahrenheit less than the freezing point of pure cannabidiol or at least27 degrees Celsius less than the freezing point of pure cannabidiol.

In some embodiments, a composition comprises cannabidiol at aconcentration of 65% to 99.5% by mass and one or more solutes selectedfrom terpenes, terpene alcohols, and terpenoids at a combinedconcentration of 0.5% to 35% by mass, in which the one or more solutesare dissolved in the cannabidiol; the composition has either a freezingpoint or a glass-liquid transition temperature; and the freezing pointor the glass-liquid transition temperature is either at least 50 degreesFahrenheit less than the freezing point of pure cannabidiol or at least27 degrees Celsius less than the freezing point of pure cannabidiol.

In some embodiments, a composition comprises cannabidiol at aconcentration of 70% to 99.5% by mass and one or more solutes selectedfrom terpenes, terpene alcohols, and terpenoids at a combinedconcentration of 0.5% to 30% by mass, in which the one or more solutesare dissolved in the cannabidiol; the composition has either a freezingpoint or a glass-liquid transition temperature; and the freezing pointor the glass-liquid transition temperature is either at least 50 degreesFahrenheit less than the freezing point of pure cannabidiol or at least27 degrees Celsius less than the freezing point of pure cannabidiol.

In some embodiments, a composition has a freezing point; the compositionlacks a glass-liquid transition temperature; and the freezing point isless than either 70 degrees Fahrenheit or 21 degrees Celsius. In somespecific embodiments, a composition has a freezing point; thecomposition lacks a glass-liquid transition temperature; and thefreezing point is less than either 60 degrees Fahrenheit or 15 degreesCelsius.

In some embodiments, a composition has a glass-liquid transitiontemperature; the composition lacks a freezing point; and theglass-liquid transition temperature is less than either 70 degreesFahrenheit or 21 degrees Celsius. In some specific embodiments, acomposition has a glass-liquid transition temperature; the compositionlacks a freezing point; and the glass-liquid transition temperature isless than either 60 degrees Fahrenheit or 15 degrees Celsius.

In some embodiments, a composition lacks crystals of cannabidiol at aconcentration greater than 5% by mass. In some specific embodiments, acomposition is essentially free of crystals of cannabidiol. In some veryspecific embodiments, a composition lacks crystals of cannabidiol.

In some embodiments, a composition comprises cannabidiol at aconcentration of 70% to 99% by mass. In some specific embodiments, acomposition comprises cannabidiol at a concentration of 75% to 95% bymass. In some very specific embodiments, a composition comprisescannabidiol at a concentration of 80% to 90% by mass.

In some embodiments, a composition lacks tetrahydrocannabinol at aconcentration greater than 0.3% by mass. In some specific embodiments, acomposition is essentially free of tetrahydrocannabinol. In some veryspecific embodiments, a composition lacks tetrahydrocannabinol.

In some embodiments, a composition comprises tetrahydrocannabinol at aconcentration greater than 0.3% by mass; the composition comprisescannabidiol and tetrahydrocannabinol at a ratio of 3:1 to 200:1 by mass;and the tetrahydrocannabinol is dissolved in the cannabidiol. In somespecific embodiments, a composition comprises tetrahydrocannabinol at aconcentration greater than 0.3% by mass; the composition comprisescannabidiol and tetrahydrocannabinol at a ratio of 4:1 to 150:1 by mass;and the tetrahydrocannabinol is dissolved in the cannabidiol. In somevery specific embodiments, a composition comprises tetrahydrocannabinolat a concentration greater than 0.3% by mass; the composition comprisescannabidiol and tetrahydrocannabinol at a ratio of 5:1 to 100:1 by mass;and the tetrahydrocannabinol is dissolved in the cannabidiol.

In some embodiments, a composition comprises(6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olat a concentration of 0.05% to 5% by mass, in which the(6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olis dissolved in cannabidiol of the composition.

In some embodiments, a composition comprises molecules having a boilingpoint lower than either 360 degrees Fahrenheit or 182 degrees Celsius ata combined concentration of at least 90% by mass. In some specificembodiments, a composition comprises molecules having a boiling pointlower than either 360 degrees Fahrenheit or 182 degrees Celsius at acombined concentration of at least 95% by mass. In some very specificembodiments, a composition comprises molecules having a boiling pointlower than either 360 degrees Fahrenheit or 182 degrees Celsius at acombined concentration of at least 98% by mass.

The term “boiling point” refers to the boiling point of a purifiedmolecule at atmospheric pressure.

In some embodiments, a composition lacks propylene glycol, glycerol,triglycerides, phospholipids, fatty acids, and waxes at a combinedconcentration greater than 10% by mass. In some specific embodiments, acomposition lacks propylene glycol, glycerol, triglycerides,phospholipids, fatty acids, and waxes at a combined concentrationgreater than 5% by mass. In some very specific embodiments, acomposition is essentially free of propylene glycol, glycerol,triglycerides, phospholipids, fatty acids, and waxes.

In some embodiments, a composition is a liquid.

In some embodiments, a composition has a viscosity, and the viscosity isless than 100 pascal-seconds at a temperature of either 70 degreesFahrenheit or 21 degrees Celsius. In some specific embodiments, acomposition has a viscosity, and the viscosity is 50 millipascal-secondsto 50 pascal-seconds at a temperature of either 70 degrees Fahrenheit or21 degrees Celsius. In some very specific embodiments, a composition hasa viscosity, and the viscosity is 0.1 pascal-seconds to 25pascal-seconds at a temperature of either 70 degrees Fahrenheit or 21degrees Celsius.

In some embodiments, a composition comprises one or more solutes, andthe one or more solutes comprise one or more of alpha-bisabolol,alpha-phellandrene, alpha-pinene, alpha-terpinene, alpha-terpineol,beta-caryophyllene, beta-pinene, borneol, cadinene, camphene, camphor,caryophyllene oxide, citral, citronellol, delta-3-carene, eucalyptol,eugenol, gamma-terpinene, geraniol, guaiol, humulene, isopulegol,limonene, linalool, myrcene, nerol, nerolidol, ocimene, para-cymene,phytol, pulegone, terpineol, terpinolene, and valencene at a combinedconcentration of 0.5% to 40% by mass. In some specific embodiments, acomposition comprises one or more solutes, and the one or more solutescomprise one or more of alpha-bisabolol, alpha-phellandrene,alpha-pinene, alpha-terpinene, alpha-terpineol, beta-caryophyllene,beta-pinene, borneol, cadinene, camphene, camphor, caryophyllene oxide,citral, citronellol, delta-3-carene, eucalyptol, eugenol,gamma-terpinene, geraniol, guaiol, humulene, isopulegol, limonene,linalool, myrcene, nerol, nerolidol, ocimene, para-cymene, phytol,pulegone, terpineol, terpinolene, and valencene at a combinedconcentration of 1% to 35% by mass.

In some embodiments, a composition comprises one or more solutes, andthe one or more solutes comprise one or more of alpha-bisabolol,beta-caryophyllene, guaiol, humulene, limonene, myrcene, and terpinoleneat a combined concentration of 0.5% to 40% by mass. In some specificembodiments, a composition comprises one or more solutes, and the one ormore solutes comprise one or more of alpha-bisabolol,beta-caryophyllene, guaiol, humulene, limonene, myrcene, and terpinoleneat a combined concentration of 1% to 35% by mass.

In some embodiments, a composition comprises cannabidiol at aconcentration of 65% to 99.5% by mass and one or more solutes, in whichthe composition lacks crystals of cannabidiol; the one or more solutesare dissolved in the cannabidiol; the one or more solutes comprise oneor more of alpha-bisabolol, beta-caryophyllene, guaiol, humulene,limonene, myrcene, and terpinolene, which are present in the compositionat a combined concentration of 0.5% to 35% by mass; the compositioncomprises molecules having a boiling point lower than either 360 degreesFahrenheit or 182 degrees Celsius at a combined concentration of atleast 95% by mass; the composition lacks tetrahydrocannabinol at aconcentration greater than 0.3% by mass; the composition lacks propyleneglycol, glycerol, triglycerides, phospholipids, fatty acids, and waxesat a combined concentration greater than 5% by mass; the composition hasa glass-liquid transition temperature; the glass-liquid transitiontemperature is less than either 70 degrees Fahrenheit or 21 degreesCelsius; the composition is a liquid; the composition lacks a freezingpoint; the composition has a viscosity; and the viscosity is 50millipascal-seconds to 50 pascal-seconds at a temperature of either 70degrees Fahrenheit or 21 degrees Celsius.

In some embodiments, a composition comprises cannabidiol at aconcentration of 65% to 99.5% by mass and one or more solutes, in whichthe composition lacks crystals of cannabidiol; the one or more solutesare dissolved in the cannabidiol; the one or more solutes comprise oneor more of alpha-bisabolol, beta-caryophyllene, guaiol, humulene,limonene, myrcene, and terpinolene, which are present in the compositionat a combined concentration of 0.5% to 35% by mass; the compositioncomprises molecules having a boiling point lower than either 360 degreesFahrenheit or 182 degrees Celsius at a combined concentration of atleast 95% by mass; the composition comprises tetrahydrocannabinol at aconcentration greater than 0.3% by mass; the tetrahydrocannabinol isdissolved in the cannabidiol; the composition comprises cannabidiol andtetrahydrocannabinol at a ratio of 3:1 to 200:1 by mass; the compositionlacks propylene glycol, glycerol, triglycerides, phospholipids, fattyacids, and waxes at a combined concentration greater than 5% by mass;the composition has a glass-liquid transition temperature; theglass-liquid transition temperature is less than either 70 degreesFahrenheit or 21 degrees Celsius; the composition is a liquid; thecomposition lacks a freezing point; the composition has a viscosity; andthe viscosity is 50 millipascal-seconds to 50 pascal-seconds at atemperature of either 70 degrees Fahrenheit or 21 degrees Celsius.

Various aspects of this patent document relate to a container comprisinga heating element and a chamber that contains a composition described inthis patent document, in which the heating element is in thermalcommunication with the composition.

Various aspects of this patent document relate to a method tomanufacture a composition described in this patent document.

In some embodiments, a method comprises providing a cannabinoidcomposition comprising cannabidiol at a concentration of 75% to 99.9% bymass; heating the cannabinoid composition to provide liquid-phasecannabidiol; providing a solute composition comprising one or moreterpenes, terpene alcohols, and terpenoids at a combined concentrationof 50% to 99.9% by mass; mixing the cannabinoid composition with thesolute composition to dissolve the one or more terpenes, terpenealcohols, and terpenoids in the liquid-phase cannabidiol; and producinga liquid cannabidiol composition, which is a composition according tothe description set forth above. In some specific embodiments, a methodcomprises providing a cannabinoid composition comprising cannabidiol ata concentration of 75% to 99.9% by mass; heating the cannabinoidcomposition to provide liquid-phase cannabidiol; providing a solutecomposition comprising one or more terpenes, terpene alcohols, andterpenoids at a combined concentration of 50% to 99.9% by mass; mixingthe cannabinoid composition with the solute composition to dissolve theone or more terpenes, terpene alcohols, and terpenoids in theliquid-phase cannabidiol; and producing a liquid cannabidiol compositioncomprising the one or more terpenes, terpene alcohols, and terpenoidsdissolved in the liquid-phase cannabidiol, in which the liquidcannabidiol composition is a liquid; the liquid cannabidiol compositioncomprises cannabidiol at a concentration of 50% to 99.5% by mass; theliquid cannabidiol composition lacks crystals of cannabidiol; the liquidcannabidiol composition has either a freezing point or a glass-liquidtransition temperature; and the freezing point or the glass-liquidtransition temperature is either less than 70 degrees Fahrenheit or lessthan 21 degrees Celsius.

In some embodiments, a cannabinoid composition is a solid at either 70degrees Fahrenheit or 21 degrees Celsius; the cannabinoid composition isa super-cooled liquid at either 70 degrees Fahrenheit or 21 degreesCelsius; or the cannabinoid composition is a liquid comprising crystalsof cannabidiol at either 70 degrees Fahrenheit or 21 degrees Celsius.

In some embodiments, a cannabinoid composition comprises crystals ofcannabidiol, and heating the cannabinoid composition melts the crystalsof cannabidiol.

In some embodiments, a liquid cannabidiol composition has a freezingpoint and lacks a glass-liquid transition temperature; and the freezingpoint is less than either 70 degrees Fahrenheit or 21 degrees Celsius.In some specific embodiments, a liquid cannabidiol composition has afreezing point and lacks a glass-liquid transition temperature; and thefreezing point is less than either 60 degrees Fahrenheit or 15 degreesCelsius.

In some embodiments, a liquid cannabidiol composition has a glass-liquidtransition temperature and lacks a freezing point; and the glass-liquidtransition temperature is less than either 70 degrees Fahrenheit or 21degrees Celsius. In some specific embodiments, a liquid cannabidiolcomposition has a glass-liquid transition temperature and lacks afreezing point; and the glass-liquid transition temperature is less thaneither 60 degrees Fahrenheit or 15 degrees Celsius. In some specificembodiments, a cannabinoid composition has a freezing point and lacks aglass-liquid transition temperature; a liquid cannabidiol compositionhas a glass-liquid transition temperature and lacks a freezing point;and the glass-liquid transition temperature of the liquid cannabidiolcomposition is less than either 70 degrees Fahrenheit or 21 degreesCelsius.

In some embodiments, a cannabinoid composition lackstetrahydrocannabinol at a concentration greater than 0.3% by mass. Insome specific embodiments, a cannabinoid composition is essentially freeof tetrahydrocannabinol. In some very specific embodiments, acannabinoid composition lacks tetrahydrocannabinol.

In some embodiments, producing a liquid cannabidiol compositioncomprises producing a liquid cannabidiol composition comprisingcannabidiol and tetrahydrocannabinol at a ratio of 3:1 to 200:1 by mass,in which the tetrahydrocannabinol is dissolved in the cannabidiol. Insome specific embodiments, producing a liquid cannabidiol compositioncomprises producing a liquid cannabidiol composition comprisingcannabidiol and tetrahydrocannabinol at a ratio of 4:1 to 150:1 by mass,in which the tetrahydrocannabinol is dissolved in the cannabidiol. Insome very specific embodiments, producing a liquid cannabidiolcomposition comprises producing a liquid cannabidiol compositioncomprising cannabidiol and tetrahydrocannabinol at a ratio of 5:1 to100:1 by mass, in which the tetrahydrocannabinol is dissolved in thecannabidiol.

In some embodiments, a cannabinoid composition comprises(6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olat a concentration of 0.05% to 5% by mass; and producing a liquidcannabidiol composition comprises producing a liquid cannabidiolcomposition comprising(6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olat a concentration of 0.05% to 5% by mass.

In some embodiments, a cannabinoid composition comprises moleculeshaving a boiling point lower than either 360 degrees Fahrenheit or 182degrees Celsius at a combined concentration of at least 95% by mass; andproducing a liquid cannabidiol composition comprises producing a liquidcannabidiol composition comprising molecules having a boiling pointlower than either 360 degrees Fahrenheit or 182 degrees Celsius at acombined concentration of at least 95% by mass.

In some embodiments, producing a liquid cannabidiol compositioncomprises producing a liquid cannabidiol composition that lackspropylene glycol, glycerol, triglycerides, phospholipids, fatty acids,and waxes at a combined concentration greater than 5% by mass. In somespecific embodiments, producing a liquid cannabidiol compositioncomprises producing a liquid cannabidiol composition that is essentiallyfree of propylene glycol, glycerol, triglycerides, phospholipids, fattyacids, and waxes. In some very specific embodiments, producing a liquidcannabidiol composition comprises producing a liquid cannabidiolcomposition that lacks propylene glycol, glycerol, triglycerides,phospholipids, fatty acids, and waxes.

In some embodiments, producing a liquid cannabidiol compositioncomprises producing a liquid cannabidiol composition that has aviscosity of less than 100 pascal-seconds at a temperature of either 70degrees Fahrenheit or 21 degrees Celsius. In some specific embodiments,producing a liquid cannabidiol composition comprises producing a liquidcannabidiol composition that has a viscosity of 50 millipascal-secondsto 50 pascal-seconds at a temperature of either 70 degrees Fahrenheit or21 degrees Celsius. In some specific embodiments, producing a liquidcannabidiol composition comprises producing a liquid cannabidiolcomposition that has a viscosity of 0.1 pascal-seconds to 25pascal-seconds at a temperature of either 70 degrees Fahrenheit or 21degrees Celsius.

In some embodiments, a cannabinoid composition has a viscosity greaterthan 25 pascal-seconds at a temperature of either 70 degrees Fahrenheitor 21 degrees Celsius; and producing a liquid cannabidiol compositioncomprises producing a liquid cannabidiol composition having a viscosityof less than 25 pascal-seconds at a temperature of either 70 degreesFahrenheit or 21 degrees Celsius.

In some embodiments, a solute composition comprises one or more ofalpha-bisabolol, alpha-phellandrene, alpha-pinene, alpha-terpinene,alpha-terpineol, beta-caryophyllene, beta-pinene, borneol, cadinene,camphene, camphor, caryophyllene oxide, citral, citronellol,delta-3-carene, eucalyptol, eugenol, gamma-terpinene, geraniol, guaiol,humulene, isopulegol, limonene, linalool, myrcene, nerol, nerolidol,ocimene, para-cymene, phytol, pulegone, terpineol, terpinolene, andvalencene at a combined concentration greater than 50% by mass; andproducing a liquid cannabidiol composition comprises producing a liquidcannabidiol composition comprising one or more of alpha-bisabolol,alpha-phellandrene, alpha-pinene, alpha-terpinene, alpha-terpineol,beta-caryophyllene, beta-pinene, borneol, cadinene, camphene, camphor,caryophyllene oxide, citral, citronellol, delta-3-carene, eucalyptol,eugenol, gamma-terpinene, geraniol, guaiol, humulene, isopulegol,limonene, linalool, myrcene, nerol, nerolidol, ocimene, para-cymene,phytol, pulegone, terpineol, terpinolene, and valencene at a combinedconcentration of 0.5% to 40% by mass. In some specific embodiments, asolute composition comprises one or more of alpha-bisabolol,alpha-phellandrene, alpha-pinene, alpha-terpinene, alpha-terpineol,beta-caryophyllene, beta-pinene, borneol, cadinene, camphene, camphor,caryophyllene oxide, citral, citronellol, delta-3-carene, eucalyptol,eugenol, gamma-terpinene, geraniol, guaiol, humulene, isopulegol,limonene, linalool, myrcene, nerol, nerolidol, ocimene, para-cymene,phytol, pulegone, terpineol, terpinolene, and valencene at a combinedconcentration greater than 90% by mass; and producing a liquidcannabidiol composition comprises producing a liquid cannabidiolcomposition comprising one or more of alpha-bisabolol,alpha-phellandrene, alpha-pinene, alpha-terpinene, alpha-terpineol,beta-caryophyllene, beta-pinene, borneol, cadinene, camphene, camphor,caryophyllene oxide, citral, citronellol, delta-3-carene, eucalyptol,eugenol, gamma-terpinene, geraniol, guaiol, humulene, isopulegol,limonene, linalool, myrcene, nerol, nerolidol, ocimene, para-cymene,phytol, pulegone, terpineol, terpinolene, and valencene at a combinedconcentration of 1% to 35% by mass.

In some embodiments, a solute composition comprises one or more ofalpha-bisabolol, beta-caryophyllene, guaiol, humulene, limonene,myrcene, and terpinolene at a combined concentration greater than 50% bymass; and producing a liquid cannabidiol composition comprises producinga liquid cannabidiol composition comprising one or more ofalpha-bisabolol, beta-caryophyllene, guaiol, humulene, limonene,myrcene, and terpinolene at a combined concentration of 0.5% to 40% bymass. In some specific embodiments, a solute composition comprises oneor more of alpha-bisabolol, beta-caryophyllene, guaiol, humulene,limonene, myrcene, and terpinolene at a combined concentration greaterthan 90% by mass; and producing a liquid cannabidiol compositioncomprises producing a liquid cannabidiol composition comprising one ormore of alpha-bisabolol, beta-caryophyllene, guaiol, humulene, limonene,myrcene, and terpinolene at a combined concentration of 1% to 35% bymass.

In some embodiments, a method comprises providing a cannabinoidcomposition comprising cannabidiol at a concentration of 75% to 99.9% bymass; heating the cannabinoid composition to provide liquid-phasecannabidiol; providing a solute composition comprising one or moreterpenes, terpene alcohols, and terpenoids at a combined concentrationof 50% to 99.9% by mass; mixing the cannabinoid composition with thesolute composition to dissolve the one or more terpenes, terpenealcohols, and terpenoids in the liquid-phase cannabidiol; and producinga liquid cannabidiol composition comprising the one or more terpenes,terpene alcohols, and terpenoids dissolved in the liquid-phasecannabidiol such that the liquid cannabidiol composition has a viscosityof less than 100 pascal-seconds at a temperature of either 70 degreesFahrenheit or 21 degrees Celsius, in which: the cannabinoid compositionhas a freezing point; the cannabinoid composition lacks a glass-liquidtransition temperature; the cannabinoid composition is either a solid, asuper-cooled liquid, or a liquid comprising crystals of cannabidiol ateither 70 degrees Fahrenheit or 21 degrees Celsius; the cannabinoidcomposition comprises molecules having a boiling point lower than either360 degrees Fahrenheit or 182 degrees Celsius at a combinedconcentration of at least 95% by mass; producing the liquid cannabidiolcomposition comprises producing a liquid cannabidiol compositioncomprising molecules having a boiling point lower than either 360degrees Fahrenheit or 182 degrees Celsius at a combined concentration ofat least 95% by mass; the liquid cannabidiol composition is a liquid;producing the liquid cannabidiol composition comprises producing aliquid cannabidiol composition that lacks propylene glycol, glycerol,triglycerides, phospholipids, fatty acids, and waxes at a combinedconcentration greater than 5% by mass; the liquid cannabidiolcomposition comprises cannabidiol at a concentration of 50% to 99.5% bymass; the liquid cannabidiol composition lacks crystals of cannabidiol;the liquid cannabidiol composition has either a freezing point or aglass-liquid transition temperature; and the freezing point or theglass-liquid transition temperature of the liquid cannabidiolcomposition is either less than 70 degrees Fahrenheit or less than 21degrees Celsius.

In some embodiments, a method comprises providing a cannabinoidcomposition comprising cannabidiol at a concentration of 75% to 99.9% bymass; heating the cannabinoid composition to provide liquid-phasecannabidiol; providing a solute composition comprising one or moreterpenes, terpene alcohols, and terpenoids at a combined concentrationof 50% to 99.9% by mass; mixing the cannabinoid composition with thesolute composition to dissolve the one or more terpenes, terpenealcohols, and terpenoids in the liquid-phase cannabidiol; and producinga liquid cannabidiol composition comprising the one or more terpenes,terpene alcohols, and terpenoids dissolved in the liquid-phasecannabidiol such that the liquid cannabidiol composition has a viscosityof less than 100 pascal-seconds at a temperature of either 70 degreesFahrenheit or 21 degrees Celsius, in which: the cannabinoid compositionhas a freezing point; the cannabinoid composition lacks a glass-liquidtransition temperature; the cannabinoid composition is either a solid, asuper-cooled liquid, or a liquid comprising crystals of cannabidiol ateither 70 degrees Fahrenheit or 21 degrees Celsius; the cannabinoidcomposition comprises molecules having a boiling point lower than either360 degrees Fahrenheit or 182 degrees Celsius at a combinedconcentration of at least 95% by mass; producing the liquid cannabidiolcomposition comprises producing a liquid cannabidiol compositioncomprising molecules having a boiling point lower than either 360degrees Fahrenheit or 182 degrees Celsius at a combined concentration ofat least 95% by mass; the liquid cannabidiol composition is a liquid;producing the liquid cannabidiol composition comprises producing aliquid cannabidiol composition that lacks propylene glycol, glycerol,triglycerides, phospholipids, fatty acids, and waxes at a combinedconcentration greater than 5% by mass; the liquid cannabidiolcomposition comprises cannabidiol at a concentration of 50% to 99.5% bymass; the liquid cannabidiol composition lacks crystals of cannabidiol;producing the liquid cannabidiol composition comprises producing aliquid cannabidiol composition that has a glass-liquid transitiontemperature and that lacks a freezing point; and the glass-liquidtransition temperature of the liquid cannabidiol composition is eitherless than 70 degrees Fahrenheit or less than 21 degrees Celsius.

Various aspects of this patent document relate to a method to administercannabidiol comprising providing a composition described in this patentdocument; heating the composition to provide at least 1 milligram ofcannabidiol vapor; and inhaling the cannabidiol vapor.

In some embodiments, a method comprises providing a compositioncomprising cannabidiol at a concentration of 65% to 99.5% by mass andone or more solutes selected from terpenes, terpene alcohols, andterpenoids at a concentration of 0.5% to 35% by mass; heating thecomposition to provide at least 1 milligram of cannabidiol vapor; andinhaling the cannabidiol vapor, in which: the composition is a liquid;the one or more solutes are dissolved in the cannabidiol; and thecomposition has either a freezing point or a gas-liquid transitiontemperature of less than either 70 degrees Fahrenheit or 21 degreesCelsius.

In some embodiments, heating a composition comprises conductivelyheating at least a portion of the composition to a temperature of atleast 330 degrees Fahrenheit or 165 degrees Celsius. In some specificembodiments, heating a composition comprises conductively heating atleast a portion of the composition to a temperature of 330 to 440degrees Fahrenheit or 165 to 227 degrees Celsius.

In some embodiments, providing a composition comprises providing acontainer containing the composition, in which the container isconfigured to position the composition in thermal communication with aheating element; and conductively heating at least a portion of thecomposition comprises transferring heat from the heating element to theportion of the composition.

In some embodiments, a method comprises positioning a composition inthermal communication with a heating element.

In some embodiments, a container comprises a chamber; the containercontains a composition within the chamber; the chamber has a volume; thecomposition has a volume; the volume of the chamber is greater than thevolume of the composition; the chamber comprises a surface thatinsulates heat and a surface that conducts heat; and positioning thecomposition in thermal communication with a heating element comprisesdirecting the composition from the surface that insulates heat to thesurface that conducts heat.

In some embodiments, a container comprises a chamber; the containercontains a composition within the chamber; the chamber comprises asurface that conducts heat; the surface that conducts heat has a surfacearea; the composition is in thermal communication with a heating elementwhen both the surface that conducts heat is in thermal communicationwith the heating element and the composition is in physical contact witha percentage of the surface area of the surface that conducts heat; thepercentage of the surface area of the surface that conducts heat that isin physical contact with the composition correlates with a rate at whichheating the composition provides cannabidiol vapor; heating thecomposition to provide at least 1 milligram of cannabidiol vapordecreases the percentage of the surface area of the surface thatconducts heat that is in physical contact with the composition; and amethod comprises directing the composition to the surface that conductsheat to increase the percentage of the surface area of the surface thatconducts heat that is in physical contact with the composition.

In some embodiments, a composition of a method has a viscosity of lessthan 100 pascal-seconds at a temperature of either 70 degrees Fahrenheitor 21 degrees Celsius. In some specific embodiments, a composition has aviscosity of 50 millipascal-seconds to 50 pascal-seconds at atemperature of either 70 degrees Fahrenheit or 21 degrees Celsius. Insome very specific embodiments, a composition has a viscosity of 0.1pascal-seconds to 25 pascal-seconds at a temperature of either 70degrees Fahrenheit or 21 degrees Celsius.

In some embodiments, a composition of a method has a gas-liquidtransition temperature, the composition lacks a freezing point, and thegas-liquid transition temperature is less than either 70 degreesFahrenheit or 21 degrees Celsius. In some specific embodiments, acomposition has a gas-liquid transition temperature, the compositionlacks a freezing point, and the gas-liquid transition temperature isless than either 60 degrees Fahrenheit or 15 degrees Celsius.

In some embodiments, a composition of a method has a freezing point, thecomposition lacks a gas-liquid transition temperature, and the freezingpoint is less than either 70 degrees Fahrenheit or 21 degrees Celsius.In some embodiments, a composition has a freezing point, the compositionlacks a gas-liquid transition temperature, and the freezing point isless than either 60 degrees Fahrenheit or 15 degrees Celsius.

In some embodiments, a composition of a method lacks propylene glycol,glycerol, triglycerides, phospholipids, fatty acids, and waxes at acombined concentration greater than 5% by mass. In some specificembodiments, a composition is essentially free of propylene glycol,glycerol, triglycerides, phospholipids, fatty acids, and waxes. In somevery specific embodiments, a composition lacks propylene glycol,glycerol, triglycerides, phospholipids, fatty acids, and waxes.

In some embodiments, a composition of a method comprises moleculeshaving a boiling point lower than either 360 degrees Fahrenheit or 182degrees Celsius at a combined concentration of at least 90% by mass. Insome specific embodiments, a composition comprises molecules having aboiling point lower than either 360 degrees Fahrenheit or 182 degreesCelsius at a combined concentration of at least 95% by mass. In somevery specific embodiments, a composition comprises molecules having aboiling point lower than either 360 degrees Fahrenheit or 182 degreesCelsius at a combined concentration of at least 98% by mass.

In some embodiments, a composition of a method lackstetrahydrocannabinol at a concentration greater than 0.3% by mass. Insome specific embodiments, a composition is essentially free oftetrahydrocannabinol. In some very specific embodiments, a compositionlacks tetrahydrocannabinol.

In some embodiments, a composition of a method comprises cannabidiol andtetrahydrocannabinol at a ratio of 3:1 to 200:1 by mass, in which thetetrahydrocannabinol is dissolved in the cannabidiol. In some specificembodiments, a composition comprises cannabidiol andtetrahydrocannabinol at a ratio of 4:1 to 150:1 by mass, in which thetetrahydrocannabinol is dissolved in the cannabidiol. In some veryspecific embodiments, a composition comprises cannabidiol andtetrahydrocannabinol at a ratio of 5:1 to 100:1 by mass, in which thetetrahydrocannabinol is dissolved in the cannabidiol.

In some embodiments, a composition of a method comprises(6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olat a concentration of 0.05% to 5% by mass, in which the(6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olis dissolved in cannabidiol of the composition.

In some embodiments, a composition of a method comprises one or moresolutes comprising one or more of alpha-bisabolol, alpha-phellandrene,alpha-pinene, alpha-terpinene, alpha-terpineol, beta-caryophyllene,beta-pinene, borneol, cadinene, camphene, camphor, caryophyllene oxide,citral, citronellol, delta-3-carene, eucalyptol, eugenol,gamma-terpinene, geraniol, guaiol, humulene, isopulegol, limonene,linalool, myrcene, nerol, nerolidol, ocimene, para-cymene, phytol,pulegone, terpineol, terpinolene, and valencene at a combinedconcentration of 0.5% to 40% by mass. In some specific embodiments, acomposition of a method comprises one or more solutes comprising one ormore of alpha-bisabolol, alpha-phellandrene, alpha-pinene,alpha-terpinene, alpha-terpineol, beta-caryophyllene, beta-pinene,borneol, cadinene, camphene, camphor, caryophyllene oxide, citral,citronellol, delta-3-carene, eucalyptol, eugenol, gamma-terpinene,geraniol, guaiol, humulene, isopulegol, limonene, linalool, myrcene,nerol, nerolidol, ocimene, para-cymene, phytol, pulegone, terpineol,terpinolene, and valencene at a combined concentration of 1% to 35% bymass.

In some embodiments, a composition of a method comprises one or moresolutes, and the one or more solutes comprise one or more ofalpha-bisabolol, beta-caryophyllene, guaiol, humulene, limonene,myrcene, and terpinolene at a combined concentration of 0.5% to 40% bymass. In some specific embodiments, a composition comprises one or moresolutes, and the one or more solutes comprise one or more ofalpha-bisabolol, beta-caryophyllene, guaiol, humulene, limonene,myrcene, and terpinolene at a combined concentration of 1% to 35% bymass.

In some embodiments, a method to administer cannabidiol comprisesproviding a container containing a composition comprising cannabidiol ata concentration of 60% to 99.5% by mass and one or more solutes selectedfrom terpenes, terpene alcohols, and terpenoids at a concentration of0.5% to 40% by mass; heating the composition to provide at least 1milligram of cannabidiol vapor; and inhaling the cannabidiol vapor, inwhich: the composition is a liquid; the composition has a viscosity ofless than 50 pascal-seconds at a temperature of either 70 degreesFahrenheit or 21 degrees Celsius; the one or more solutes are dissolvedin the cannabidiol; the composition comprises molecules having a boilingpoint lower than either 360 degrees Fahrenheit or 182 degrees Celsius ata combined concentration of at least 95% by mass; the composition lackspropylene glycol, glycerol, triglycerides, phospholipids, fatty acids,and waxes at a combined concentration greater than 5% by mass; thecomposition has either a freezing point or a gas-liquid transitiontemperature of less than either 70 degrees Fahrenheit or 21 degreesCelsius; the container is configured to position the composition inthermal communication with a heating element; heating the compositioncomprises conductively heating at least a portion of the composition toa temperature of at least 330 degrees Fahrenheit or 165 degrees Celsius;and conductively heating at least a portion of the composition comprisestransferring heat from the heating element to the portion of thecomposition.

In some embodiments, a method to administer cannabidiol comprisesproviding a container containing a composition comprising cannabidiol ata concentration of 60% to 99.5% by mass and one or more solutes selectedfrom one or more of alpha-bisabolol, beta-caryophyllene, guaiol,humulene, limonene, myrcene, and terpinolene at a combined concentrationof 0.5% to 40% by mass; heating the composition to provide at least 1milligram of cannabidiol vapor; and inhaling the cannabidiol vapor, inwhich: the composition is a liquid; the composition has a viscosity ofless than 50 pascal-seconds at a temperature of either 70 degreesFahrenheit or 21 degrees Celsius; the one or more solutes are dissolvedin the cannabidiol; the composition comprises molecules having a boilingpoint lower than either 360 degrees Fahrenheit or 182 degrees Celsius ata combined concentration of at least 95% by mass; the composition lackspropylene glycol, glycerol, triglycerides, phospholipids, fatty acids,and waxes at a combined concentration greater than 5% by mass; thecomposition has either a freezing point or a gas-liquid transitiontemperature of less than either 70 degrees Fahrenheit or 21 degreesCelsius; the container is configured to position the composition inthermal communication with a heating element; heating the compositioncomprises conductively heating at least a portion of the composition toa temperature of at least 330 degrees Fahrenheit or 165 degrees Celsius;and conductively heating at least a portion of the composition comprisestransferring heat from the heating element to the portion of thecomposition.

The following examples provide a framework to implement certain aspectsof the disclosure, and these examples do not limit the scope of thispatent document or any claim that matures from the disclosure of thispatent document.

EXEMPLIFICATION Example 1. Production of Compositions ComprisingCannabidiol that do not Crystallize

Cannabinoids were extracted from organic industrial hemp using thesystem described in PCT Patent Application Publication No. 2016/161420A1 to produce crude industrial hemp extract comprising 65-70%cannabidiol; 5-10% terpenes, terpene alcohols, and terpenoids; 2-3%tetrahydrocannabinol; and other volatile molecules including waxes andphospholipids. The crude industrial hemp extract formed crystals ofcannabidiol when stored at room temperature for 24 hours.

The cannabinoids of the crude industrial hemp extract were separatedfrom other molecules by distillation in a VTA Short Path DistillationPlant VKL 70 (Verfahrenstechnische Anlagen GmbH & Co. KG, Germany) toproduce a cannabinoid distillate comprising approximately 90%cannabidiol and 5% tetrahydrocannabinol. 10 grams of the cannabinoiddistillate was combined with 0.1 grams of a terpene, terpene alcohol,and terpenoid blend obtained from True Terpenes (Oregon, USA) withheating to produce a liquid composition. The blend containedbeta-caryophyllene (41%), humulene (18%), linalool (13%), limonene,alpha-bisabolol, nerolidol, beta-pinene, citronellol, fenchol, and othermolecules at lower concentrations.

The liquid composition was stored at room temperature for 1 year withintermittent exposure to light and air, and the composition produced nodetectable crystals. Cooling the liquid below room temperature vitrifiedthe composition into a glass without any detectable crystal formation.

This example demonstrates that small amounts of terpenes, terpenealcohols, and terpenoids can provide robust stabilization of cannabidiolin a liquid state and inhibit crystal formation overcommercially-relevant timeframes, even when subjected to chemicalstress, provided that lipids that comprise fatty acids are removed fromthe liquid state.

What is claimed is:
 1. A method to manufacture a composition,comprising: providing a cannabinoid composition comprising cannabidiolat a concentration of 75% to 99.9% by mass; heating the cannabinoidcomposition to provide liquid-phase cannabidiol; providing a solutecomposition comprising one or more terpenes, terpene alcohols, andterpenoids at a combined concentration of 50% to 99.9% by mass; mixingthe cannabinoid composition with the solute composition to dissolve theone or more terpenes, terpene alcohols, and terpenoids in theliquid-phase cannabidiol; and producing a liquid cannabidiol compositioncomprising the one or more terpenes, terpene alcohols, and terpenoidsdissolved in the liquid-phase cannabidiol, in which: the liquidcannabidiol composition is a liquid; the liquid cannabidiol compositioncomprises cannabidiol at a concentration of 50% to 99.5% by mass; theliquid cannabidiol composition lacks crystals of cannabidiol; the liquidcannabidiol composition has either a freezing point or a glass-liquidtransition temperature; and the freezing point or the glass-liquidtransition temperature is either less than 70 degrees Fahrenheit or lessthan 21 degrees Celsius.
 2. A container, comprising a heating elementand a chamber that contains a composition, in which: the heating elementis in thermal communication with the composition; the compositioncomprises cannabidiol at a concentration of 50% to 99.5% by mass; thecomposition comprises one or more solutes selected from terpenes,terpene alcohols, and terpenoids at a concentration of 0.5% to 40% bymass; the one or more solutes are dissolved in the cannabidiol; thecomposition has either a freezing point or a glass-liquid transitiontemperature; and the freezing point or the glass-liquid transitiontemperature is less than either 70 degrees Fahrenheit or 21 degreesCelsius.
 3. A method to administer cannabidiol, comprising: providing acomposition comprising cannabidiol at a concentration of 60% to 99.5% bymass and one or more solutes selected from terpenes, terpene alcohols,and terpenoids at a concentration of 0.5% to 40% by mass, in which thecomposition is a liquid, the one or more solutes are dissolved in thecannabidiol, and the composition has either a freezing point or agas-liquid transition temperature of less than either 70 degreesFahrenheit or 21 degrees Celsius; heating the composition to provide atleast 1 milligram of cannabidiol vapor; and inhaling the cannabidiolvapor.
 4. A composition, comprising cannabidiol at a concentration of50% to 99.5% by mass and one or more solutes selected from terpenes,terpene alcohols, and terpenoids at a combined concentration of 0.5% to40% by mass, in which: the one or more solutes are dissolved in thecannabidiol; the composition has either a freezing point or aglass-liquid transition temperature; and the freezing point or theglass-liquid transition temperature is either at least 50 degreesFahrenheit less than the freezing point of pure cannabidiol or at least27 degrees Celsius less than the freezing point of pure cannabidiol. 5.The composition of claim 4, in which: the composition has a freezingpoint; the composition lacks a glass-liquid transition temperature; andthe freezing point is less than either 70 degrees Fahrenheit or 21degrees Celsius.
 6. The composition of claim 4, in which: thecomposition has a glass-liquid transition temperature; the compositionlacks a freezing point; and the glass-liquid transition temperature isless than either 70 degrees Fahrenheit or 21 degrees Celsius.
 7. Thecomposition of claim 4, in which the composition lacks crystals ofcannabidiol.
 8. The composition of claim 4, in which the compositioncomprises cannabidiol at a concentration of 75% to 99% by mass.
 9. Thecomposition of claim 4, in which the composition lackstetrahydrocannabinol at a concentration greater than 0.3% by mass. 10.The composition of claim 4, in which: the composition comprisestetrahydrocannabinol at a concentration greater than 0.3% by mass; thetetrahydrocannabinol is dissolved in the cannabidiol; and thecomposition comprises cannabidiol and tetrahydrocannabinol at a ratio of3:1 to 200:1 by mass.
 11. The composition of claim 4, comprising(6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olat a concentration of 0.05% to 5% by mass, in which the(6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olis dissolved in the cannabidiol.
 12. The composition of claim 4, inwhich the composition comprises molecules having a boiling point lowerthan either 360 degrees Fahrenheit or 182 degrees Celsius at a combinedconcentration of at least 95% by mass.
 13. The composition of claim 4,in which the composition lacks propylene glycol, glycerol,triglycerides, phospholipids, fatty acids, and waxes at a combinedconcentration greater than 5% by mass.
 14. The composition of claim 4,in which the composition is a liquid.
 15. The composition of claim 14,in which the composition has a viscosity, and the viscosity is less than100 pascal-seconds at a temperature of either 70 degrees Fahrenheit or21 degrees Celsius.
 16. The composition of claim 15, in which theviscosity is 50 millipascal-seconds to 50 pascal-seconds at atemperature of either 70 degrees Fahrenheit or 21 degrees Celsius. 17.The composition of claim 4, in which the one or more solutes compriseone or more of alpha-bisabolol, alpha-phellandrene, alpha-pinene,alpha-terpinene, alpha-terpineol, beta-caryophyllene, beta-pinene,borneol, cadinene, camphene, camphor, caryophyllene oxide, citral,citronellol, delta-3-carene, eucalyptol, eugenol, gamma-terpinene,geraniol, guaiol, humulene, isopulegol, limonene, linalool, myrcene,nerol, nerolidol, ocimene, para-cymene, phytol, pulegone, terpineol,terpinolene, and valencene at a combined concentration of 0.5% to 40% bymass.
 18. The composition of claim 4, in which the one or more solutescomprise one or more of alpha-bisabolol, beta-caryophyllene, guaiol,humulene, limonene, myrcene, and terpinolene at a combined concentrationof 0.5% to 40% by mass.
 19. The composition of claim 4, in which: thecomposition comprises cannabidiol at a concentration of 65% to 99% bymass; the composition lacks crystals of cannabidiol; the compositionlacks tetrahydrocannabinol at a concentration greater than 0.3% by mass;the one or more solutes comprise one or more of alpha-bisabolol,beta-caryophyllene, guaiol, humulene, limonene, myrcene, and terpinoleneat a combined concentration of 0.5% to 35% by mass; the compositioncomprises molecules having a boiling point lower than either 360 degreesFahrenheit or 182 degrees Celsius at a combined concentration of atleast 95% by mass; the composition lacks propylene glycol, glycerol,triglycerides, phospholipids, fatty acids, and waxes at a combinedconcentration greater than 5% by mass; the composition has aglass-liquid transition temperature; the glass-liquid transitiontemperature is less than either 70 degrees Fahrenheit or 21 degreesCelsius; the composition lacks a freezing point; the composition is aliquid; and the composition has a viscosity, and the viscosity is 50millipascal-seconds to 50 pascal-seconds at a temperature of either 70degrees Fahrenheit or 21 degrees Celsius.
 20. The composition of claim4, in which: the composition comprises cannabidiol at a concentration of65% to 99% by mass; the composition lacks crystals of cannabidiol; thecomposition comprises tetrahydrocannabinol at a concentration greaterthan 0.3% by mass; the tetrahydrocannabinol is dissolved in thecannabidiol; the composition comprises cannabidiol andtetrahydrocannabinol at a ratio of 3:1 to 200:1 by mass; the one or moresolutes comprise one or more of alpha-bisabolol, beta-caryophyllene,guaiol, humulene, limonene, myrcene, and terpinolene at a combinedconcentration of 0.5% to 35% by mass; the composition comprisesmolecules having a boiling point lower than either 360 degreesFahrenheit or 182 degrees Celsius at a combined concentration of atleast 95% by mass; the composition lacks propylene glycol, glycerol,triglycerides, phospholipids, fatty acids, and waxes at a combinedconcentration greater than 5% by mass; the composition has aglass-liquid transition temperature; the glass-liquid transitiontemperature is less than either 70 degrees Fahrenheit or 21 degreesCelsius; the composition lacks a freezing point; the composition is aliquid; and the composition has a viscosity, and the viscosity is 50millipascal-seconds to 50 pascal-seconds at a temperature of either 70degrees Fahrenheit or 21 degrees Celsius.